# US 8,772,320 B2 · Nicotinamide derivative or salt thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,772,320 B2
- Document ID: US8772320B2
- Status: Granted
- Kind: B2
- Application number: 13/730,000
- Filed: 2012-12-28
- Published: 2013-05-09
- Granted: 2014-07-08
- Earliest claimed: 2010-06-30
- Assignees: FUJIFILM Corporation
- Applicants: Hideyasu Fujiwara; Kimihiko Sato; Shinsuke Mizumoto; Yuichiro Sato; Hideki Kurihara; Yohei Kubo; Hiyoku Nakata; Yasutaka Baba; Takashi Tamura; Hidenobu Kuniyoshi; Shinji Hagiwara; Mari Yamamoto
- Inventors: Hideyasu Fujiwara; Kimihiko Sato; Shinsuke Mizumoto; Yuichiro Sato; Hideki Kurihara; Yohei Kubo; Hiyoku Nakata; Yasutaka Baba; Takashi Tamura; Hidenobu Kuniyoshi; Shinji Hagiwara; Mari Yamamoto
- Web page: https://patentgrep.com/patent/US8772320B2

## Abstract

An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. The present invention provides a nicotinamide derivative represented by the following formula (I) (wherein R1 represents a halogen atom; R2 represents a C1-12 alkyl group, a C2-12 alkenyl group, a C2-12 alkynyl group, a C3-8 cycloalkyl group, an aryl group, an ar-C1-6 alkyl group or a heterocyclic group, each optionally having at least one substituent; R3 represents an aryl group or a heterocyclic group each optionally having at least one substituent; and R4 and R5 each independently represent a hydrogen atom; and R2 and R4 may form a cyclic amino group optionally having at least one substituent together with the nitrogen atom to which they bind) or a salt thereof, and a pharmaceutical composition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

## Claims

### Claim 1

A nicotinamide derivative represented by the following formula (I) or a salt thereof:
wherein
R1 represents a halogen atom;
R2 represents a C1-12 alkyl group optionally having at least one substituent, a C2-12 alkenyl group optionally having at least one substituent, a C2-12 alkynyl group optionally having at least one substituent, a C3-8 cycloalkyl group optionally having at least one substituent, an aryl group optionally having at least one substituent, an ar-C1-6 alkyl group optionally having at least one substituent or a heterocyclic group optionally having at least one substituent;
R3 represents an aryl group optionally having at least one substituent or a heterocyclic group optionally having at least one substituent; and
R4 and R5 each independently represent a hydrogen atom, a C1-12 alkyl group, a C2-12 alkenyl group, or a C2-12 alkynyl group;
wherein the substituent optionally possessed by the C1-12 alkyl group, C2-12 alkenyl group, C2-12 alkynyl group, C3-8 cycloalkyl group, aryl group, ar-C1-6 alkyl group or heterocyclic group, represented by R2, is selected from the following substituent group α1-2, wherein
the substituent group α1-2 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected hydroxyl group; an optionally protected amino group; a C1-6 alkyl group optionally having at least one substituent selected from the following substituent group β1-1; a C2-6 alkenyl group optionally having at least one substituent selected from the following substituent group β1-1; a C2-6 alkynyl group optionally having at least one substituent selected from the following substituent group β1-1; a C3-8 cycloalkyl group optionally having at least one substituent selected from the following substituent group β1-1; an aryl group optionally having at least one substituent selected from the following substituent group β1-1; a C1-6 alkoxy group optionally having at least one substituent selected from the following substituent group β1-1; an aryloxy group optionally having at least one substituent selected from the following substituent group β1-1; an acyl group optionally having at least one substituent selected from the following substituent group β1-1; a C1-6 alkylsulfonyl group optionally having at least one substituent selected from the following substituent group β1-1; an arylsulfonyl group optionally having at least one substituent selected from the following substituent group β1-1; a heterocyclic group optionally having at least one substituent selected from the following substituent group β1-1; and a group represented by the formula -Q1-Q2-NR6R7 (wherein R6 and R7 each independently represent a hydrogen atom, an amino-protecting group, a C1-6 alkyl group optionally having at least one substituent, a C2-6 alkenyl group optionally having at least one substituent, a C2-6 alkynyl group optionally having at least one substituent, a C3-8 cycloalkyl group optionally having at least one substituent, a C1-6 alkoxy group optionally having at least one substituent, an aryl group optionally having at least one substituent, or a heterocyclic group optionally having at least one substituent, or R6 and R7 may form a cyclic amino group optionally having at least one substituent, together with the nitrogen atom to which they bind; Q1 represents —NH—, a C1-6 alkylene group optionally having at least one substituent, a C2-6 alkenylene group optionally having at least one substituent, a C2-6 alkynylene group optionally having at least one substituent, or a bond; Q2 represents a group represented by —C(═X7)— (wherein X7 represents an oxygen atom, a sulfur atom, or a group represented by ═NR29 (wherein R29 represents a hydrogen atom, a C1-12 alkyl group optionally having at least one substituent, a C2-12 alkenyl group optionally having at least one substituent, a C2-12 alkynyl group optionally having at least one substituent, a C3-8 cycloalkyl group optionally having at least one substituent or a C1-6 alkoxy group optionally having at least one substituent)), a C1-6 alkylene group, or a bond),
wherein the substituent group β1-1 consists of a halogen atom, a cyano group, a nitro group, an oxo group, an optionally protected carboxyl group, an optionally protected hydroxyl group, an optionally protected amino group, a C1-6 alkyl group optionally having at least one halogen atom, a C3-8 cycloalkyl group optionally having at least one halogen atom, a C1-6 alkoxy group optionally having at least one halogen atom, an aryl group optionally having at least one halogen atom, and a heterocyclic group optionally having at least one halogen atom;
wherein the substituent optionally possessed by the aryl or heterocyclic group represented by R3 is selected from the following substituent group α2-2,
wherein the substituent group α2-2 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected hydroxyl group; an optionally protected amino group; a C1-6 alkyl group optionally having at least one substituent selected from the following substituent group β2-1; a C2-6 alkenyl group optionally having at least one substituent selected from the following substituent group β2-1; a C2-6 alkynyl group optionally having at least one substituent selected from the following substituent group β2-1; a C3-8 cycloalkyl group optionally having at least one substituent selected from the following substituent group β2-1; an aryl group optionally having at least one substituent selected from the following substituent group β2-1; a C1-6 alkoxy group optionally having at least one substituent selected from the following substituent group β2-1; an aryloxy group optionally having at least one substituent selected from the following substituent group β2-1; an acyl group optionally having at least one substituent selected from the following substituent group β2-1; a C1-6 alkylsulfonyl group optionally having at least one substituent selected from the following substituent group β2-1; an arylsulfonyl group optionally having at least one substituent selected from the following substituent group β2-1; a heterocyclic group optionally having at least one substituent selected from the following substituent group β2-1; and a group represented by the formula -Q3-Q4-NR24R25 (wherein R24 and R25 each independently represent a hydrogen atom, an amino-protecting group, a C1-6 alkyl group optionally having at least one substituent, a C2-6 alkenyl group optionally having at least one substituent, a C2-6 alkynyl group optionally having at least one substituent, a C3-8 cycloalkyl group optionally having at least one substituent, a C1-6 alkoxy group optionally having at least one substituent, an ar-C1-6 alkyl group optionally having at least one substituent, an aryl group optionally having at least one substituent, a heterocyclic group optionally having at least one substituent, or R24 and R25 may form a cyclic amino group optionally having at least one substituent, together with the nitrogen atom to which they bind; Q3represents —NH—, a C1-6 alkylene group optionally having at least one substituent, a C2-6 alkenylene group optionally having at least one substituent, a C2-6 alkynylene group optionally having at least one substituent, or a bond; and Q4 represents —C(═O)—, a C1-6 alkylene group, or a bond);
wherein the substituent group β2-1 consists of a halogen atom, a cyano group, a nitro group, an oxo group, an optionally protected carboxyl group, an optionally protected hydroxyl group, an optionally protected amino group, a C1-6 alkyl group optionally having at least one halogen atom, a C3-8 cycloalkyl group optionally having at least one halogen atom, a C1-6 alkoxy group optionally having at least one halogen atom, an ar-C1-6 alkyl group optionally having at least one halogen atom, an aryl group optionally having at least one halogen atom, and a heterocyclic group optionally having at least one halogen atom;
wherein the heterocyclic group is selected from the group consisting of azetidinyl, pyrrolidinyl, pyrrolinyl, pyrrolyl, piperidyl, tetrahydropyridyl, pyridyl, homopiperidinyl, octahydroazocinyl, imidazolidinyl, imidazolinyl, imidazolyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, piperazinyl, pyrazinyl, pyridazinyl, pyrimidinyl, homopiperazinyl, triazolyl, tetrazolyl, tetrahydrofuranyl, furanyl, tetrahydropyranyl, pyranyl, thienyl, oxazolyl, isoxazolyl, oxadiazolyl, morpholinyl, thiazolyl, isothiazolyl, thiadiazolyl, thiomorpholinyl, 1-oxide-thiomorpholinyl, 1,1-dioxide-thiomorpholinyl, indolinyl, indolyl, isoindolinyl, isoindolyl, benzimidazolyl, indazolyl, benzotriazolyl, quinolyl, tetrahydroquinolinyl, quinolyl, tetrahydroisoquinolinyl, isoquinolinyl, quinolizinyl, cinnolinyl, phthalazinyl, quinazolinyl, dihydroquinoxalinyl, quinoxalinyl, naphthyridinyl, pyrrolopyridyl, imidazopyridyl, indolidinyl, dihydrocyclopentapyridyl, triazolopyridyl, pyrazolopyridyl, pyridopyrazyl, purinyl, pteridinyl, quinuclidinyl, 2,3-dihydrobenzofuranyl, benzofuranyl, isobenzofuranyl, chromanyl, chromenyl, isochromanyl, 1,3-benzodioxolyl, 1,3-benzodioxanyl, 1,4-benzodioxanyl, 2,3-dihydrobenzothienyl, benzothienyl, benzoxazolyl, benzoisoxazolyl, benzoxadiazolyl, benzomorpholinyl, dihydropyranopyridyl, dihydrodioxinopyridyl, 1,3-dioxolopyridyl, dihydropyridooxazinyl, benzothiazolyl, benzoisothiazolyl, benzothiadiazolyl and thiazolopyridyl; and
wherein the acyl group is a formyl group, a succinyl group, a glutaryl group, a maleoyl group, a phthaloyl group, a C2-12 alkanoyl group, an aroyl group, or an (α-substituted) amino acetyl group.

### Claim 2 (depends on 1, 2)

The nicotinamide derivative or a salt thereof according to claim 1, wherein the substituent optionally possessed by the C1-12 alkyl group, C2-12 alkenyl group, C2-12 alkynyl group, C3-8 cycloalkyl group, aryl group, ar-C1-6 alkyl group or heterocyclic group, represented by R2, is selected from the following substituent group α1-3, wherein
the substituent group α1-3 consists of a cyano group; an oxo group; an optionally protected hydroxyl group; an optionally protected amino group; an aryl group optionally having at least one substituent selected from the following substituent group β1-2; a C1-6 alkoxy group optionally having at least one substituent selected from the following substituent group β1-2; a heterocyclic group optionally having at least one substituent selected from the following substituent group β1-2; and a group represented by the formula -Q1-Q2-NR6R7 (wherein Q1, Q2, R6 and R7 each have the same definitions as those described in claim 2);
wherein the substituent group β1-2 consists of a halogen atom and an optionally protected amino group.

### Claim 3 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein R2 represents a C1-12 alkyl group having, as a substituent, an optionally protected amino group or a heterocyclic group optionally having at least one substituent, or a C3-8 cycloalkyl group having, as a substituent, an optionally protected amino group or a heterocyclic group optionally having at least one substituent.

### Claim 4 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein R2 is a substituent represented by any one of the following formulae (II) to (V) and (VII):
wherein R10, R11, R12, R13,R16, R17, R18, R20 and R21 each independently represent a hydrogen atom, or a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, aryl, C1-6 alkoxy, aryloxy, acyl, C1-6 alkylsulfonyl, arylsulfonyl or heterocyclic group, each optionally having at least one substituent, R14, R15, R19 and R30 each independently represent a hydrogen atom, or a C1-6 alkyl or acyl group, X8 represents an oxygen atom, a sulfur atom or ═NR23 (wherein R23 represents a hydrogen atom, or a C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-8 cycloalkyl or C1-6 alkoxy group), R22 represents a heterocyclic group, X9 and X10each independently represent an oxygen atom, —NR31— (wherein R31 represents a hydrogen atom, or a C1-12 alkyl, C2-12 alkenyl, C2-12alkynyl, C3-8 cycloalkyl, C1-6 alkoxy, acyl, C1-6 alkoxycarbonyl, aryloxycarbonyl or heterocyclic oxycarbonyl group), or a methylene group (wherein either one of X9 and X10 represents a methylene group, and when m3 is 0, X10 represents a methylene group), m1 and m3 each independently represent an integer from 0 to 2, m2 represents an integer of 1 or 2, wherein R20 and R21 may be different from each other when m2 is 2, n represents an integer from 0 to 4, R16s may be different from one another when n is 2 to 4, and wherein R10 and R11, R12 and R13, R17 and R18, and R20 and R21 may each together form a C3-8 cycloalkyl or heterocyclic group, each optionally having at least one substituent;
wherein the substituent is selected from the following substituent group γ1-1,
wherein the substituent group γ1-1 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected hydroxyl group; an optionally protected amino group; a C1-6 alkyl, C3-8 cycloalkyl or heterocyclic group; and the formula -Q5-Q6-NR27R28 (wherein R27 and R28 each independently represent a hydrogen atom; an amino-protecting group; or a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C1-6 alkoxy, aryl or heterocyclic group; Q5 represents —NH—; a C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene group; or a bond; and Q6 represents —C(═O)—, a C1-6 alkylene group or a bond).

### Claim 5 (depends on 4)

The nicotinamide derivative or a salt thereof according to claim 4, wherein R2 is a substituent represented by the following formula (II-1):
wherein R32 and R33 each independently represent a hydrogen atom, or a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, aryl, C1-6 alkoxy, aryloxy, acyl, C1-6 alkylsulfonyl, arylsulfonyl or heterocyclic group, each optionally having at least one substituent selected from the following substituent group γ1-2, wherein
the substituent group γ1-2 consists of a halogen atom, and C1-6 alkyl, C3-8 cycloalkyl, aryl and heterocyclic groups.

### Claim 6 (depends on 5)

The nicotinamide derivative or a salt thereof according to claim 5, wherein R32 represents an alkyl group; an alkyl group substituted with a cycloalkyl group; a cycloalkyl group; or a cycloalkyl group substituted with an alkyl group, each containing 3 to 5 carbon atoms in total, or an alkoxyalkyl group containing 2 to 4 carbon atoms in total.

### Claim 7 (depends on 5)

The nicotinamide derivative or a salt thereof according to claim 5, wherein R32 represents a methyl or ethyl group substituted with a heterocyclic group.

### Claim 8 (depends on 5)

The nicotinamide derivative or a salt thereof according to claim 5, wherein R33 represents a hydrogen atom, or a C1-6 alkyl or C3-8 cycloalkyl group.

### Claim 9 (depends on 4)

The nicotinamide derivative or a salt thereof according to claim 4, wherein R2 is a substituent represented by the following (III-4):

### Claim 10 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein R4 and R5 each represent a hydrogen atom.

### Claim 11 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, which is represented by the following formula (I-1):
wherein R26 is a substituent represented by any one of the above formulae (II) to (V) and (VII), and R3 has the same definitions as those described in claim 1.

### Claim 12 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein the aryl group or the heterocyclic group of the aryl group or the heterocyclic group each optionally having at least one substituent, represented by R3, is a phenyl, pyridyl, pyridazinyl, quinoxalinyl or indazolyl group.

### Claim 13 (depends on 12)

The nicotinamide derivative or a salt thereof according to claim 12, wherein the aryl group or the heterocyclic group of the aryl group or the heterocyclic group each optionally having at least one substituent, represented by R3, is a pyridyl, quinoxalinyl or indazolyl group.

### Claim 14 (depends on 1, 9)

The nicotinamide derivative or a salt thereof according to claim 1, wherein the substituent optionally possessed by the aryl or heterocyclic group represented by R3 is selected from the following substituent group α2-3, wherein the substituent group α2-3 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected amino group; a C1-6 alkyl group optionally having at least one substituent selected from the following substituent group β2-2; a C3-8 cycloalkyl group optionally having at least one substituent selected from the following substituent group β2-2; an aryl group optionally having at least one substituent selected from the following substituent group β2-2; a C1-6 alkoxy group optionally having at least one substituent selected from the following substituent group β2-2; an aryloxy group optionally having at least one substituent selected from the following substituent group β2-2; an acyl group optionally having at least one substituent selected from the following substituent group β2-2; a C1-6 alkylsulfonyl group optionally having at least one substituent selected from the following substituent group β2-2; a heterocyclic group optionally having at least one substituent selected from the following substituent group β2-2; and a group represented by the formula -Q3-Q4-NR24R25 (wherein Q3, Q4, R24 and R25 each have the same definitions as those described in claim 9); wherein
the substituent group β2-2 consists of a halogen atom, an optionally protected hydroxyl group, a C1-6 alkyl group optionally having at least one halogen atom, a C3-8 cycloalkyl group optionally having at least one halogen atom, a C1-6 alkoxy group optionally having at least one halogen atom, an aryl group optionally having at least one halogen atom, and a heterocyclic group optionally having at least one halogen atom.

### Claim 15 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein R3 represents a pyridyl group optionally having a substituent selected from the following substituent group α2-4, wherein
the substituent group α2-4 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected hydroxyl group; an optionally protected amino group; a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, aryl, C1-6 alkoxy, aryloxy, acyl, C1-6 alkylsulfonyl, arylsulfonyl or heterocyclic group, each optionally having at least one substituent selected from the following substituent group β2-3; and the formula -Q3-Q4-NR24R25 (wherein Q3, Q4, R24 and R25 have the same definitions as those described above); wherein
the substituent group β2-3 consists of a halogen atom; a cyano group; a nitro group; an oxo group; an optionally protected carboxyl group; an optionally protected hydroxyl group; an optionally protected amino group; and a C1-6 alkyl, C3-8 cycloalkyl, -Q5m4-R36 (wherein Q5 represents a C1-6 alkyleneoxy group (wherein the R36 side is an alkylene group), R36 represents a hydrogen atom, or a C1-6 alkyl, C3-8 cycloalkyl, aryl or heterocyclic group, m4represents an integer from 1 to 3, and Q5s may be different from one another when m4 is 2 or 3), aryl, or heterocyclic group, each optionally having at least one halogen atom.

### Claim 16 (depends on 15)

The nicotinamide derivative or a salt thereof according to claim 15, wherein R3 represents a pyridyl group represented by the following formula (VIII-1) or (VIII-2):
wherein R37, R38, R39, R40, R41, R42, R43 and R44 each independently represent a hydrogen atom, or a substituent selected from the following substituent group α2-6; wherein
the substituent group α2-6 consists of a halogen atom; and a C1-6 alkyl, C3-8 cycloalkyl, aryl, C1-6 alkoxy or heterocyclic group, each optionally having at least one substituent selected from the following substituent group β2-5; wherein
the substituent group β2-5 consists of a halogen atom; and a C1-6 alkyl, C3-8 cycloalkyl, -Q5m4-R36 (wherein Q5, R36, and m4have the same definitions as those described above), aryl or heterocyclic group, each optionally having at least one halogen atom.

### Claim 17 (depends on 16)

The nicotinamide derivative or a salt thereof according to claim 16, wherein R3 represents a pyridyl group represented by the following formula (VIII-3) or (VIII-4):
wherein R45, R46, R47 and R48 each independently represent a hydrogen atom, or a substituent selected from the above-described substituent group α2-6.

### Claim 18 (depends on 17)

The nicotinamide derivative or a salt thereof according to claim 17, wherein R45 represents a 5-membered ring heterocyclic group optionally having at least one substituent selected from among a halogen atom, C1-6 alkyl, C3-8 cycloalkyl, and -Q5m4-R36 (wherein Q5, R36, and m4have the same definitions as described above), and R48 represents a halogen atom, a C1-6 alkyl group or a C1-6 alkoxy group.

### Claim 19 (depends on 17)

The nicotinamide derivative or a salt thereof according to claim 17, wherein R45 represents a halogen atom; or a C1-6 alkyl or C1-6 alkoxy group optionally having at least one halogen atom, and R46 represents a 5-membered ring or 6-membered ring heterocyclic group, each optionally having at least one substituent selected from among a halogen atom, C1-6 alkyl, C3-8 cycloalkyl, and -Q5m4-R36 (wherein Q5, R36, and m4have the same definitions as those described above).

### Claim 20 (depends on 17)

The nicotinamide derivative or a salt thereof according to claim 17, wherein R47 and R48 each independently represent a hydrogen atom; a halogen atom; or a C1-6 alkyl, aryl, C1-6 alkoxy or heterocyclic group, each optionally having at least one substituent independently selected from among a halogen atom, C1-6 alkyl, C3-8 cycloalkyl and -Q5m4-R36 (wherein Q5, R36, and m4have the same definitions as those described above).

### Claim 21 (depends on 15)

The nicotinamide derivative or a salt thereof according to claim 15, wherein R3 represents an indazolyl group represented by any one of the following formulae (IX-1) to (IX-6):
wherein R49, R50, R51, R52, R53, R54, R55, R56, R57, R58, R59, R60, R61, R62, R63, R64, R65, R66, R67, R68, R69, R70, R71, R72, R73, R74, R75, R76, R77 and R78 each independently represent a hydrogen atom, or a substituent selected from the above-described substituent group α2-6.

### Claim 22 (depends on 21)

The nicotinamide derivative or a salt thereof according to claim 21, wherein R3 represents an indazolyl group represented by the following formula (IX-7) or (IX-8):
wherein R79, R80, R81 and R82 each independently represent a hydrogen atom, or a substituent selected from the above-described substituent group α2-6.

### Claim 23 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein the formula (I) is represented by the following formula (I-2):
wherein R83, R84, R85 and R86 each independently represent a hydrogen atom, or a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, aryl, C1-6 alkoxy, aryloxy, acyl, C1-6 alkylsulfonyl, arylsulfonyl or heterocyclic group, each optionally having at least one substituent, R87 has the same definitions as those of R3 described in claim 1, wherein R83 and R84, and R85 and R86 may each together form a C3-8 cycloalkyl or heterocyclic group, each optionally having at least one substituent.

### Claim 24 (depends on 1)

The nicotinamide derivative or a salt thereof according to claim 1, wherein the formula (I) is represented by the following formula (I-6):
wherein R94 has the same definitions as those of R3 described in claim 1.

### Claim 25 (depends on 1)

A pharmaceutical composition comprising the nicotinamide derivative or a salt thereof according to claim 1.

### Claim 26 (depends on 25)

A method for the treatment of a Syk-related disease, comprising administering the pharmaceutical composition of claim 25 to a patient in need thereof, wherein the disease is selected from the group consisting of rheumatism and idiopathic thrombocytopenic purpura.

### Claim 27

A compound which is selected from the group consisting of:
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-phenylpyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(3-methylphenylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(4-(morpholin-4-yl)phenylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(3,4,5-trimethoxyphenylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methoxypyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(2,6-dimethoxypyridin-4-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-(morpholin-4-yl)pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(6-(morpholin-4-yl)pyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(pyrimidin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1,5-naphthyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1,6-naphthyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1,6-naphthyridin-8-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(8-nitroquinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-c]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrolo[2,3-c]pyridin-4-ylamino)nicotinamide;
2-(8-acetylaminoquinolin-3-ylamino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-(anilinocarbonyl)pyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
methyl 5-(3-aminocarbonyl-6-(cis-2-aminocyclohexylamino)-5-fluoropyridin-2-ylamino)nicotinate;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(6-methylpyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methylpyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrolo[2,3-b]pyridin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-(morpholin-4-yl)ethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-([1,3]thiazolo[4,5-b]pyridin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1-(2-(diethylamino)ethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-isobutyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-(2H-1,2,3-triazol-2-yl)pyridin-3-ylamino)-nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-(1H-pyrrol-2-yl)pyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-(2-thienyl)pyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(5-cyclopropylpyridin-3-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-(2-furyl)pyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(8-aminoquinolin-3-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1H-pyrrolo[2,3-c]pyridin-4-ylamino)nicotinamide;
2-(8-(aminocarbonyl)aminoquinolin-3-ylamino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(2-aminoethylamino)-5-fluoro-2-(pyridin-4-ylamino)nicotinamide;
6-(2-aminoethylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(2,1,3-benzothiadiazol-5-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1,3-benzothiazol-6-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-indazol-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methyl-1,3-benzoxazol-6-ylamino)nicotinamide;
6-(2-aminoethylamino)-2-(1,3-benzothiazol-6-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methyl-1,3-benzoxazol-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-methylpyridin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-5-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(3-(2H-1,2,3-triazol-2-yl)phenylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(6-methoxyquinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinolin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinoxalin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(1,3-benzothiazol-5-ylamino)-5-fluoronicotinamide;
6-(2-aminoethylamino)-5-fluoro-2-(isoquinolin-4-ylamino)nicotinamide;
6-(2-aminoethylamino)-5-fluoro-2-(quinolin-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-indazol-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-benzoimidazol-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinazolin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinazolin-7-ylamino)nicotinamide;
cis-6-(2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-benzoimidazol-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methylquinolin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinolin-7-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-methyl-1H-indazol-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-methylquinoxalin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(2-(2-(pyrrolidin-1-yl)ethyl)-2H-indazol-5-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1H-indazol-5-ylamino)nicotinamide;
6-(2-aminoethylamino)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(3-chlorophenylamino)-5-fluoronicotinamide;
6-(2-aminoethylamino)-5-fluoro-2-(quinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(isoquinolin-4-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(1,8-naphthyridin-3-ylamino)nicotinamide;
5-fluoro-6-(2-(1H-imidazol-5-yl)ethylamino)-2-(quinolin-3-ylamino)nicotinamide;
6-((1R)-2-amino-2-oxo-1-phenylethylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2R)-1-amino-4-methyl-1-oxopentan-2-ylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2R)-1-amino-1-oxobutan-2-ylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2S)-2-aminobutylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2S)-2-amino-3-methylbutylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2S)-2-amino-2-phenylethylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2R)-2-amino-3-methoxypropylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2S)-2-aminopropylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-((2S)-2-amino-4-methylpentylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-(3-aminopropylamino)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide;
6-((1R,2S)-2-aminocyclohexylamino)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-chloro-2-(quinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-bromo-2-(quinolin-3-ylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-chloro-2-(3-methoxyphenylamino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-chloro-2-(5-methylpyridin-3-ylamino)nicotinamide; and
6-(cis-2-aminocyclohexylamino)-5-bromo-2-(5-methylpyridin-3-ylamino)nicotinamide.

### Claim 28

A compound which is selected from the group consisting of:
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(6-methylpyridin-3-ylamino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((5-cyano-6-morpholinopyridin-3-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-(5-methylpyridin-3-ylamino)nicotinamide;
(R)-6-((1-amino-4-methylpentan-2-yl)amino)-5-fluoro-2-((quinolin-6-yl)amino)nicotinamide;
(R)-6-((1-amino-4-methylpentan-2-yl)amino)-5-fluoro-2-((2-(2-methoxyethoxy)pyridin-4-yl)amino)nicotinamide ;
6-((1R,2S)-2-aminocyclohexylamino)-5-fluoro-2-((6-morpholinopyridin-3-yl)amino)nicotinamide;
2-((5-(1H-pyrazol-1-yl)pyridin-3-yl)amino)-6-((1R,2S)-2-aminocyclohexylamino)-5-fluoronicotinamide;
(R)-6-((1-amino-4-methylpentan-2-yl)amino)-2-((5,6-dimethylpyridin-3-yl)amino)-5-fluoronicotinamide;
6-(((2S,3R)-2-aminopentane3-yl)amino)-2-((1-ethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(((2S,3R)-2-aminohexane3-yl)amino)-5-fluoro-2-((2-methoxypyridin-4-yl)amino)nicotinamide;
6-(((2S,3R)-2-aminopentane3-yl)amino)-5-fluoro-2-((5-(2-fluorophenyl)pyridin-3-yl)amino)nicotinamide;
6-(((2S,3R)-2-aminopentane3-yl)amino)-5-fluoro-2-((1-methoxyisoquinolin-6-yl)amino)nicotinamide;
6-(((2S,3R)-2-aminopentane3-yl)amino)-5-fluoro-2-((1-methyl-1H-indazol-4-yl)amino)nicotinamide;
6-(((2S,3R)-2-aminohexane3-yl)amino)-2-((5,6-dimethylpyridin-3-yl)amino)-5-fluoronicotinamide;
6-(((2S,3R)-2-aminohexane3-yl)amino)-5-fluoro-2-((5-fluoropyridin-3-yl)amino)nicotinamide;
6-(((2S,3R)-2-aminohexane3-yl)amino)-5-fluoro-2-((2-propoxypyridin-4-yl)amino)nicotinamide;
(R)-6-((1-amino-4-methylpentan-2-yl)amino)-2-((1-ethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(((2R,3S)-3-amino-1-cyclopropylbutan-2-yl)amino)-2-((1-ethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(((1R,2S)-2-amino-1-cyclopropylpropyl)amino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide;
6-(((1R,2S)-2-aminocyclohexyl)amino)-5-fluoro-2(6-methyl-5-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)amino)nicotinamide;
6-(((1R,2S)-2-aminocyclohexyl)amino)-5-fluoro-2-((6-methoxy-5-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)amino)nicotinamide;
6-(((2S,3R)-2-amino-5-methylhexane3-yl)amino)-5-fluoro-2-((1-methyl-1H-indazol-5-yl)amino)nicotinamide;
6-(((2S,3R)-2-amino-5-methylhexane3-yl)amino)-2-((1-ethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(((1R,2S)-2-aminocyclohexyl)amino)-5-fluoro-2-((5-fluoro-6-morpholinopyridin-3-yl)amino)nicotinamide;
6-(((1R,2S)-2-aminocyclohexyl)amino)-2((2-ethoxy-3-fluoropyridin-4-yl)amino)-5-fluoronicotinamide;
6-(((2R,3S)-3-amino-1-cyclopropylbutan-2-yl)amino)-2-((5,6-dimethylpyridin-3-yl)amino)-5-fluoronicotinamide;
6-(((2S,3S)-3-amino-1-methoxybutan-2-yl)amino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide; and
6-(2-aminoethylamino)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide.

### Claim 29

A compound which is selected from the group consisting of:
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((6-methyl-5-phenylpyridin-3-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((5,6-dimethylpyridin-3-yl)amino)-5-fluoronicotinamide;
2-(1H-indazol-4-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((1-(2-morpholinoethyl)-1H-indazol-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((1-(cyclopropylmethyl)-1H-indazol-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((1-(2-methoxyethyl)-1H-indazol-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((1(2-(2-ethoxyethoxy)ethyl)-1H-indazol-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(cyclopropylmethyl)-2H-indazol-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2((2-benzyl-2H-indazol-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2(2-(2-methoxyethyl)-2H-indazol-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2((2-benzyl-2H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((5-ethylpyridin-3-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2(2-methyl-2H-indazol-5-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((1-(cyclopropylmethyl)-1H-indazol-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((1-(2-methoxyethyl)-1H-indazol-6-yl)amino)nicotinamide;
2-(2-(1H-pyrrol-2-yl)pyridin-4-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-phenylpyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(furan-2-yl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-isopropoxypyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(furan-3-yl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(methylamino)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(2-ethoxypyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-(2,6-diethoxypyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((5-(5-methylfuran-2-yl)pyridin-3-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-((5-methylfuran-2-yl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-methoxy-6-phenylpyridin-4-yl) amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-methoxyethoxy)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-morpholino-6-phenylpyridin-4-yl)amino)nicotinamide;
2-((5-(1H-pyrazol-4-yl)pyridin-3-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
2-(2-(1H-pyrazol-4-yl)pyridin-4-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-propoxypyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-butoxypyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-isobutoxypyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-methoxyquinolin-7-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-methoxyethoxy)quinolin-7-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-((1-methoxypropan-2-yl)oxy)quinolin-7-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(3-methoxybutoxy)quinolin-7-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2-(2-ethoxyethoxy)ethoxy)quinolin-7-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((5-(1-cyclohexen-1-yl)pyridin-3-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-methoxyethoxy)quinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-((1-methoxypropan-2-yl)oxy)quinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(3-methoxybutoxy)quinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2-(2-ethoxyethoxy)ethoxy)quinolin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-methoxyquinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-ethoxyquinolin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-propoxyquinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2-ethoxyethoxy)quinolin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-(2-methoxyethoxy)ethoxy)quinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-((tetrahydrofuran-2-yl)methoxy)quinolin-6-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-(2-oxopyrrolidin-1-yl)ethoxy)quinolin-6-yl)amino)nicotinamide;
2-((2-(1H-1,2,4-triazol-1-yl)pyridin-4-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((5-(furan-3-yl)-6-methylpyridin-3-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2,3-dimethoxyquinoxalin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2,3-diethoxyquinoxalin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((4-methyl-3,4-dihydro-2H-[1,4]oxazino[2,3-b]quinoxalin-7-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2,3-dimethylquinoxalin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2,3-diethylquinoxalin-6-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((1-ethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((1-propyl-1H-indazol-5-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-fluorophenyl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2,4-difluorophenyl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((6-methyl-5-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)amino)nicotinamide;
2-((5-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-fluoro-3-methoxyphenyl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-fluoro-4-methoxyphenyl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(2-fluoro-5-methoxyphenyl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((6-cyclopropylpyridin-3-yl)amino)-5-fluoronicotinamide;
2-((3-(1H-pyrazol-1-yl)quinolin-7-yl)amino)-6-(cis-2-aminocyclohexylamino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2,3-difluorophenyl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(2,5-difluorophenyl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(3-chloro-2-fluorophenyl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-((5-chloro-2-fluorophenyl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((5-(benzo[d][1,3]dioxol-5-yl)pyridin-3-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-2-((2-(benzo[d][1,3]dioxol-5-yl)pyridin-4-yl)amino)-5-fluoronicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((5-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)pyridin-3-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(3-methoxyphenyl)pyridin-4-yl)amino)nicotinamide;
6-(cis-2-aminocyclohexylamino)-5-fluoro-2-((2-(4-methoxyphenyl)pyridin-4-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-ethyl-1H-indazol-6-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-ethyl-1H-indazol-4-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-(2,2-difluoroethyl)-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-(2,2-difluoroethyl)-1H-indazol-6-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((5-(quinolin-7-yl)pyridin-3-yl) amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((5-(isoquinolin-6-yl)pyridin-3-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((5-(isoquinolin-7-yl)pyridin-3-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((2-(quinolin-7-yl)pyridin-4-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((2-(isoquinolin-6-yl)pyridin-4-yl) amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((2-(isoquinolin-7-yl)pyridin-4-yl)amino)nicotinamide;
6-(((cis)-2-aminocyclohexyl)amino)-2-((benzofuro[2,3-b]pyridin-3-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((3-fluoro-1-methyl-1H-indazol-5-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-ethyl-3-fluoro-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((3-fluoro-1-methyl-1H-indazol-6-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-ethyl-3-fluoro-1H-indazol-6-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((1-(2-fluoroethyl)-1H-indazol-5-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((1-(2-fluoroethyl)-1H-indazol-6-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((3-fluoro-1-(2-fluoroethyl)-1H-indazol-5-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((3-fluoro-1-(2-fluoroethyl)-1H-indazol-6-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1,3-dimethyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-2-((1-ethyl-3-methyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((1-(2-methoxyethyl)-3-methyl-1H-indazol -5-yl)amino)nicotinamide;
6-((cis-2-aminocyclohexyl)amino)-5-fluoro-2-((1-(2-fluoroethyl)-3-methyl-1H-indazol-5-yl)amino)nicotinamide; and
6-((cis-2-aminocyclohexyl)amino)-2-((1-(2,2-difluoroethyl)-3-methyl-1H-indazol-5-yl)amino)-5-fluoronicotinamide.